Growth Leadership – Leadership program + portal + CEO community + vendor-neutral intelligence for scaling SMBs.
Tier B • Growth Leadership

Growth Leadership
Leadership Program + Portal for Scaling SMB CEOs

Growth Leadership is for CEOs with teams in the 10–50+ employee range who want a structured leadership program around IT – combining a strategy portal, curated bi-weekly CEO strategy sessions and vendor-neutral intelligence – before stepping into full 1:1 executive advisory.

Investment (USD) Popular for 10–50 staff

$795 / month

or $7,950 / year

One avoided bad project or unnecessary renewal typically covers the entire year. Growth Leadership gives CEOs neutral guidance, structured reviews and ongoing IT decision support — without relying on your MSP for strategy.

  • Deep-dive review of your IT spend and tools (once/year)
  • Vendor proposals translated into plain English with red flags marked
  • Guidance on renewals, licensing, and cost traps
  • Quarterly check-ins on roadmap, priorities and risks
  • Ad-hoc review of incidents or surprise outages
Book a Call About Growth Leadership

What you get with Growth Leadership

Everything in Essentials, plus the leadership program:
  • Full access to the IT Strategy Portal and all Essentials content
  • CEO-only online community and discussion hub – no MSPs or vendors
  • Bi-weekly CEO Strategy Sessions (AMA format, 60–90 minutes) where we walk through selected member questions and live examples
  • Monthly Vendor Intelligence Brief – short, practical analysis of vendor behaviour, pricing and contract tactics we’re seeing in the field
  • Monthly CEO Strategic Decision Briefing – 2–3 page PDF on one key decision area (e.g. “Do we renew this MSP?”, “Is now the time for a cloud move?”, “What’s enough cyber for our size?”)
  • Quarterly Peer Insights Benchmark – anonymous roll-up of spend, risk, cloud adoption and incident patterns across the club
  • Early access to new executive toolkits – Growth members see new templates, checklists and scripts first
  • Vendor quote assessment (1 per month) with a simple green/yellow/red summary and 3–5 line rationale
  • Annual MSP contract sanity check for reasonableness and obvious gaps
  • Annual IT maturity & risk snapshot – based on a structured executive questionnaire, with a clear score and prioritized fixes
How the bi-weekly CEO strategy sessions work
  • Sessions run every two weeks for approximately 60–90 minutes
  • CEOs submit questions in advance through the portal; submissions close Friday at 5:00 PM for the following week’s session
  • Questions are curated and selected to cover a mix of cost, risk, vendor and roadmap topics that benefit the widest range of members
  • We use real-world examples (sanitized) to keep the discussion grounded in business outcomes, not jargon
  • Growth members can watch live or on replay, and apply the insights to their own situation

Why CEOs choose Growth Leadership:

  • They want a structured leadership program around IT, not just ad-hoc advice
  • They like seeing patterns across peers instead of making decisions in isolation
  • They want to avoid expensive missteps on big decisions (cloud, MSP, security) while keeping 1:1 advisory optional
  • They value an independent, vendor-neutral voice in the mix

Is Growth Leadership the right fit?

Good fit if:

  • You’re responsible for a growing team (10–50+ people) and IT is now board-visible.
  • You want a structured way to improve IT decisions over the next 12–24 months.
  • You anticipate cloud migrations, security upgrades or system changes in that window.
  • You like having a group of peers and vendor-neutral intel to sanity-check decisions with.

Consider Executive Advisory instead if:

  • You want a monthly 1:1 call dedicated solely to your environment and situation.
  • You have multiple vendors and high-impact projects already in motion.
  • Your board or lenders are actively asking IT-related questions and deadlines are firm.
Ask Whether Growth or Advisory Fits Better

Optional executive add-ons

These are one-time or per-instance engagements that can be added to any membership tier. We’ll always recommend the smallest option that genuinely fits your situation. Growth members often pair their membership with a Spend Baseline & Savings Map or Incident Tabletop in the first 6–12 months.

IT Spend Baseline & Savings Map

One-time review of your current IT spend (MSP, licenses, connectivity, backup, security) with a simple visual of where the money goes and 3–5 concrete savings opportunities.

  • Consolidate overlapping tools & services
  • Spot “auto-renew” traps and surprise costs
  • Map spend to business functions and risk

From $3,250 USD (up to ~50–75 staff). Larger environments priced by scope.

Board / Lender IT Briefing (Virtual)

A focused, plain-English briefing for your board or lender on current IT posture, key risks, and the short list of actions you are taking next.

  • Pre-call to understand your priorities & politics
  • Concise virtual briefing with Q&A
  • Short written summary you can reuse

From $3,750 USD per briefing. On-site board sessions available by request.

Incident / Ransomware Tabletop

Scenario-based exercise with your leadership team to walk through who does what, in what order, and with what information when something goes wrong.

  • Custom scenario tuned to your reality
  • Facilitated 90–120 minute live session
  • Gap list and next-step recommendations

From $2,750 USD per exercise (virtual). Hybrid and on-site options available.

On-Site Strategy Day

One day on-site with your CEO, leadership team and key IT stakeholders to align roadmap, spend, and risk with your actual business plans.

  • Pre-session call to shape the agenda
  • Full-day working session on-site
  • Written summary & 90-day action outline

From $5,250 USD plus travel (capped). Available to Advisory & Counsel members first.

Policy & Minimum Controls Pack

Lightweight tuning of core policies and minimum controls so you can demonstrate “reasonable steps” to staff, partners and insurers.

  • Acceptable use & remote work policy tuning
  • Backup / MFA / password baseline guidance
  • Light customization for your environment

From $1,950 USD one-time, depending on complexity and number of locations.

Note: All add-ons are scoped and confirmed in writing before any work begins. No long-term commitment is required beyond your selected membership tier.

Give yourself a structured CEO peer program for IT decisions.

Growth Leadership combines the structure of the portal with curated CEO strategy sessions and vendor-neutral intelligence – so you can make stronger IT decisions without yet committing to full 1:1 counsel.